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Updated Oct 14, 202426 Cute Winter Date Night Outfits for Guys and Girls
Dresses, pants, shirts and skirts sure to bring the heat to your cold-weather date night.
Choosing what to wear for date night—be it a blind first date or a special night out with your spouse—can be difficult. Selecting a cute winter date night outfit is even tougher. You have to ride a fine line: sexy and stylish, but still warm. And what you wear says a lot about you: Especially on a first date, it's your initial opportunity to make a statement about your personality. For your winter-months dating wardrobe, we suggest starting with the location. Will it be a romantic ice-rink rendezvous? Cozy and cuddly movie on the couch? Holiday party or fancy night on the town? The winter weather vibe and venue should dictate your direction—from there, infuse your personal style. Here we've rounded up cute cold-weather date outfits for men and women to spark some inspiration.
In this article:
Winter Date Night Outfits for Women
Winter is the season to sparkle! Be it literally—like with a pair of fully sequined pants—or figuratively, let your personality shine through your choice of winter date night outfit. Consider fun and festive cold-weather date ideas—from skiing and drinking hot cocoa, to holiday parties and hot yoga—when picking what to wear.
Torrid Midi Sequin Skirt
Midi skirts are all the rage right now—and we're here for it. And what's not to love about this style? It's full of sparkle to bring a bright spot to the dreary season, but in a comfortable high rise silhouette available up to size 30. Pair these with a roomy sweater for something upscale-casual, or go full glam with a matching sequined tee and blazer.
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Saylor NYC Angellina Dress
The perfect sweater dress doesn't exi—wait. Maybe it does. This slouchy turtleneck sweater dress features cable knit braids on the top and a chic slit in the midi length skirt. Wear it with knee-high boots for a warm and stylish ensemble for a casual date.
Heartloom Kenly Sweater
A simple white sweater, dressed up with detail. Pair this with jeans to dress it down for a night at the movies, or chic ivory trousers and heels for the perfect winter whites ensemble.
LoveShackFancy X Bogner Ilvy Quarter Zip in Rosemary Mauve
Nothing says winter romance like a ski or snowboarding date. Take your love to the mountains in fashion-forward pieces from this LoveShackFancy collab, which boasts snow pants, puffer jackets and matching warm layers underneath. We love this floral first layer, even off the slopes—it makes the perfect outfit for warming up to each other.
Reformation Cashmere Polo Sweater
What could be more fitting for date night than a relaxed-fit polo sweater? This cozy cashmere version comes in a variety of color combos (and stripes!) and is made for cuddling on the couch with a bowl of popcorn while snow falls outside the window—or at least, that's what we're wearing it for. Bonus: the oversized sweater's recycled cashmere fabric is totally sustainable.
BCBGeneration Faux Leather Jumpsuit
We love a hunter green look for the winter months, and this animal-friendly faux leather jumpsuit can do double duty as a casual movie-night look or dressed up for an evening on the town.
Show Me Your Mumu Lombardi Long Cardi
Any piece that can be worn multiple ways gets bonus points in our book, and this long fur-trimmed cardigan is the perfect example. Wear it as your jacket with a fall outfit when the weather is mild, over jeans and a tank for a casual dinner or overtop a mini dress for a fancier affair. It comes in three neutral hues—we're getting them all!
Line & Dot Riley Long Sleeve
A chic off-the-shoulder top shows just the right amount of skin for that first date. Pair it with brown leather pants for a cool monochromatic look.
Eloquii Colorblock Sweater Cardigan Dress
Spice up the typical sweater dress with this colorblocked cardigan version, versatile enough to wear as a dress or pop on over jeans and wear open. We love the black and white for something classic and the two-tone red for the holiday season, but the coming-soon colorway of ocean cavern and argan oil is our top pick for a casual date night.
J.Crew Faux-Feather-Trim Cotton Poplin Button-Up Shirt with Collar
Classic, with a twist—just like you. J.Crew has refreshed its aesthetic recently and we're loving the new direction. This feather-trimmed button-down comes in a variety of colors (try the pale seascape blue) and looks equally as cool with jeans and a blazer, or a skirt and over the knee boots.
Free People Christa Sequin Long Sleeve Romper
One thing we love to embrace about winter style is the glitz: It's the best season for sequins, sparkles, and glam. This mini wrap "dress" has all that, a pop of color and a surprise: While it looks like a mini skirt, it's actually a romper! Wear it to a holiday party or dress up date night.
Sachin & Babi Charmaine Sweater
For a look that transitions seamlessly from work to a dinner date—and braves the elements in between—pair a chicly bedazzled sweater with a pencil skirt and booties. We love this Sachin & Babi style with chandelier-inspired crystal detailing. It's a splurge, but one you can wear again and again.
Altar'd State Lora Dress
Blend in with the holiday decor through your date night look—or, rather, outshine it—in this stylish puff sleeve dress with a dark floral pattern. Its trendy sweetheart neckline would perfectly frame a statement necklace, and heeled ankle boots would finish the look.
ASOS Design Tux Suit in Ivory
We're all about winter whites, especially in a tuxedo-inspired suit like this one from ASOS. The pants and blazer can be worn on their own or together; for a sexy take, don a lacy cami under the blazer and add a glittering necklace.
Esther & Co. Bentelene Knit Dress in Chocolate
A warm chocolate brown knit dress is just the thing for a hot cocoa date. Pair this one with bright white sneakers to match the cutout piping for a casual day date, then swap to heels when your date inevitably carries over into the evening.
Winter Date Night Outfits for Men
We say it's always better to be overdressed—or in winter, over layered—than under. Stock your closet with cozy sweaters, shackets and sport coats that can be layered or worn alone to make your selections go even further. The below winter date night outfit ideas for guys will show off your fashionable side and make you look oh so put together—while also kicking off some conversation.
Abercrombie & Fitch Ski Graphic Crew Neck Sweater
It's the perfect conversation starter: "Do you ski?" your date will surely ask when they see the graphic logo. Each colorway touts a different dreamy ski locale: Breckenridge, Telluride, Lake Tahoe, Vail and more; choose your go-to spot or the most flattering color and let the conversation flow. Bonus: It's rendered in an ultra-soft fleece fabric, so it's warm enough to actually wear on the mountain, too.
Topman Skinny Fit Jumbo Corduroy Sport Coat
Corduroy is having a major moment this season—and it works for casual outfits or dressed up. This velvety black sport coat has peaked lapels and an ultra-wide corduroy material for a trendy twist. Wear it with jeans to dress it down, or go full out with matching pants for a big event.
NAADAM Fisherman Crewneck Sweater
Every guy needs a timeless crewneck sweater—or ten—in his wardrobe. We love the rich hues of this one for the snowy season. Layer it under a sport coat for date night, or wear it on its own.
Indochino Flaxton Corduroy Red Casual Pants
'Tis the season to embrace red, guys. Show your date you're not afraid of color in these holiday-ready corduroy pants. Indochino offers a plethora of customization options, too: You can choose button color, pocket placement, hem style and more to make these your own.
Brax Harold Hi-Flex Stretch Leaf Button-Up Shirt
Mix up the classic plaid or check and go for a bolder pattern that might just jump start a conversation. This button-up has just that, with scattered leaves in blue and gray and a crisp tailored look. Plus, the innovative material is wrinkle-resistant, so it will last all day if you're going straight from work to a dinner date.
Vince Cotton Blend Shirt Jacket
Shackets are having a moment in women's fashion, but let's be honest: We borrowed the concept from the boys. Here's a classic shirt jacket that can be worn buttoned up or open over a t-shirt, bringing the warmth—and the heat!—either way.
J. Crew Kenmare Suit Jacket in Italian Wool
The label's Kenmare range is all about laid-back suiting—ideal for a date where you want to look nice, but not too overdressed. This deep navy jacket can be worn over a sweater with jeans or paired with the fuller suit pants of the same style.
Indochino Fairwood Corduroy Olive Casual Shirt
An of-the-moment update to flannel, this corduroy material makes for the perfect winter shirt, and its dark green hue signals the season even more. Customize the cuffs, trim, pocket and length before you buy—then wear it with dark jeans and Chelsea boots.
Polo Ralph Lauren Men's Reversible Sleep Jogger Pants
So, a blizzard has canceled your date night. No worries— cozy up with your significant other on the couch instead, and turn on your favorite binge-worthy show. But first, pull on a pair of stylish joggers—these ones are reversible from heather gray to navy—to look the part.
